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    Harbor Cafe & Pizzeria

    3.7 (3 reviews)

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    15 years ago

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    13 years ago

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    The Retriever Bar and Oysters - The House Burger

    The Retriever Bar and Oysters

    4.3(40 reviews)
    14.6 mi

    This was a fun place. We came visiting friends while in town for the Tea Party weekend, so they get…read morea little pass for being busy. I'm not sure the menu was all that imaginative, but the food was good and we enjoyed some oysters, onion dip, and I had the chicken sandwich. Our waiter was very attentive. The only thing I may add is to think about better flexibility on seating. It's a very large bar but the sit down area isn't greatly configurable. We'd put in for a group of 6 but it was not possible for them to seat us all at one table.

    The Retriever Oyster House in Chestertown left us with a mixed impression, one that deserves a fair…read moreand constructive take. We had just come from a college football game and, on the fly, decided to grab dinner here based on the recommendation of the one local in our group. There were seven of us, and most went for the double smash burgers with fries, which were excellent. Kim, our server, was outstanding, prompt, accurate, and attentive throughout the evening. The bartender also added to the positive side of the experience, making sure everything at the table ran smoothly. The issue came at the door. We had tried to call ahead to let them know we were on the way, not realizing that OpenTable was their preferred system. When we arrived, the host made this clear, but in a way that was unnecessarily sharp and cold. It set the wrong tone for the night. In a town where friendliness is the norm, the contrast was striking. The experience began under a haze that was difficult to shake, even though the food and drinks were excellent once we sat down. To be constructive, this is less about policy and more about hospitality. A host sets the tone, and a welcoming explanation could have changed everything. Something as simple as, "We usually use OpenTable to handle groups this size, but I'm glad you're here, let's get you taken care of," would have gone a long way. Instead of frustration, it could have created a positive first impression and likely earned a loyal group of returning guests for years to come. Inside, the atmosphere was lively, with locals enjoying themselves in a loud and fun environment. Our group of longtime friends who have been convening in Chestertown for two decades fit right in once we were seated. However, the bad first impression lingered, and as a result we only had one round with food before deciding to leave a lot earlier than our normal rhythm for an evening out. We ended up taking our bar bill to another venue. Great food and excellent table service carried the night, but the host made sure we will not be returning as part of our annual tradition. This is a restaurant with strong potential, and it could go from good to exceptional with just a little more attention to how guests are greeted.

    Photos
    The Retriever Bar and Oysters - The bar

    The bar

    The Retriever Bar and Oysters - Apple strudel

    Apple strudel

    The Retriever Bar and Oysters - Shrimp & Grits

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    Shrimp & Grits

    The Restaurants At Wyncote - Flatbread and meatballs

    The Restaurants At Wyncote

    3.9(11 reviews)
    31.3 mi

    A great dining experience with incredible views. This is a restaurant located in a golf course, but…read moreit is open to the public. As soon as you enter the driveway it is the building on the right. For some reason our GPS was showing that it was a different building that wasn't able to be accessed by car. There is ample parking and a very relaxed dress code. There is a lounge/lobby area outside of the restaurant with comfortable seating and tables so you can grab a drink and wait for a table if needed. They do take reservations. The dining room has several tables and even a rather large table for a party of 12 in the center. There is a bar area with high top seating as well. There was live music (this was a weekend evening) that was great. The view from the restaurant is great as it overlooks the golf course. All staff were very attentive and helpful. We were seated immediately by the hostess and the server greeted us quickly. Throughout our visit, the staff were wonderful. The drinks were great. Some crafty cocktail concoctions are on the menu. The only concern was the whisky ice cube served in the sidecar - easily able to remove it though so no harm done (it was tasty). The apps were good too. The mushroom soup was delicious and get the homemade meatballs! Highly recommend - ask for extra bread to use all of the delicious sauce served with them. The calamari is great as it also has shishito peppers and cherry peppers served with it and the flavor combination of those three are great. The flatbread was also good. Overall, very good food. Wonderful option for tasty food and lovely views.

    The blackened shrimp Alfredo was excellent. My wife ordered the steak frites and it was average…read more The previous way the restaurant use to make it was much better when they serviced the steak with a peppercorn sauce and the thick cut fries. The service was great. My complaint and why I gave it three stars was the noise! There was a singer playing and his music was way too loud. (And not very good, in my opinion). I could not even hear my wife who was sitting next to me. We could not wait to get out of there. In fact the next table told the waitress they wanted their check because of the noise.

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    The Restaurants At Wyncote - Live music

    Live music

    The Restaurants At Wyncote
    The Restaurants At Wyncote - Water

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    Water

    Water Street Seafood - Shrimp po boy

    Water Street Seafood

    4.4(291 reviews)
    17.1 mi
    $$$
    Family-owned & operated
    Locally owned & operated

    This place was amazing. Small venue feel, amazing service, food was so flavorful. Snow crab…read moreamazing, steak frittes amazing. 100% recommend this place. Its hard to find this kind of passion In dining industry.

    I had a wonderful experience dining here. We made reservations for an outside table at lunch. Since…read morewe were hungry for seafood, we ordered several things: 1/2 pound of shrimp, fresh grilled fish, crab hush puppies, raw oysters and clams. Everything was great. Probably my favorite things were the crab hush puppies, and the fresh fish, served with pineapple. The entrees came with two sides. Therefore, I tried four sides. The French fries and potato salad were really good. The fresh vegetables had onions in it. I am not a big onion fan. The coleslaw was good. Next time, I will order the fish, with just one side- the potato salad was very large. For an appetizer, I will get the clams again, and the crab hush puppies. Yelp was so helpful guiding me to the hush puppies. The chef prepared our food outstandingly. Coral was are very friendly server. A nice meal with an outstanding server and a view of the water made for an excellent day. The host and the people helping out to clear the table were very nice, also. The vibe at the restaurant was a tropical beach feeling. People were dressed casually, mostly in t-shirts.

    Photos
    Water Street Seafood - The dining indoor dining room.

    The dining indoor dining room.

    Water Street Seafood - This is half of the Chesapeake cheesesteak sandwich! Yumm!

    This is half of the Chesapeake cheesesteak sandwich! Yumm!

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    Harbor Cafe & Pizzeria - restaurants - Updated August 2026

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